Unknown

Dataset Information

0

Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hy-droxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta[a]phenanthren-17-yl]-N-meth-oxy-N-methyl-pro-pan-amide (Fernholz Weinreb amide).

ABSTRACT: The literature compound 3?-hy-droxy-bis-nor-5-cholenic aldehyde is an important inter-mediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important inter-mediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3?-hy-droxy-bis-nor-5-cholenic acid. The title amide crystallized with two mol-ecules in the asymmetric unit, linked into helices by O-H?O hydrogen bonds involving the hy-droxy and carbonyl groups.

SUBMITTER: Viktorsson EO 

PROVIDER: S-EPMC4350737 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Crystal structure of (S)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-hy-droxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta[a]phenanthren-17-yl]-N-meth-oxy-N-methyl-pro-pan-amide (Fernholz Weinreb amide).

Viktorsson Elvar Ørn EØ   Åstrand Ove Alexander Høgmoen OA   Haseeb Rasha Sabah RS   Görbitz Carl Henrik CH   Rongved Pål P  

Acta crystallographica. Section E, Crystallographic communications 20150218 Pt 3

The literature compound 3β-hy-droxy-bis-nor-5-cholenic aldehyde is an important inter-mediate for the synthesis of new modulators of the nuclear oxysterol receptor Liver X. As part of our ongoing search for new LXR antagonists, the title compound, C24H39NO3, has proven to be an important inter-mediate in our new synthetic pathway, giving the corresponding aldehyde in high yield and in only three steps from the commercially available 3β-hy-droxy-bis-nor-5-cholenic acid. The title amide crystalliz  ...[more]

Similar Datasets

Unknown (8S,9R,10S,11S,13S,14S,16S,17R)-4,4-Dichloro-16?-methyl-3,20-dioxo-17,21-bis-(propano-yloxy)-5?,8?-epoxy-pregna-1,9-diene.
| S-EPMC2970074 | biostudies-literature
Unknown (1R,2R,5R,6R,9S,10S,13S,14S)-1,6,7,8,9,14,15,16,17,17-Decachloro-penta-cyclo-[12.2.1.1.0.0]octa-deca-7,15-diene.
| S-EPMC2961698 | biostudies-literature
Unknown (8S,9S,10R)-4-(4-Chloro-benz-yloxy)-7,8-didehydro-3,7-dimeth-oxy-17-methyl-morphinan-6-one monohydrate.
| S-EPMC3089213 | biostudies-literature
Unknown Ethyl (1R,4S,5R,9S,10R,13S)-5,9,13-trimethyl-14-methyl-ene-14-oxotetra-cyclo-[11.2.1.0.0]hexa-decane-5-carboxyl-ate.
| S-EPMC2980194 | biostudies-literature
Unknown (4R,5R,6S,7R,8S,9R,10S,13S)-7,8β-Epoxy-momilactone-A.
| S-EPMC2961202 | biostudies-literature
Unknown 10,13-Dimethyl-16-oxo-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetra-deca-hydro-1H-cyclo-penta-[a]phenanthren-17-yl acetate.
| S-EPMC3007217 | biostudies-literature
Unknown (1S,2S,3R,4S,5R,7S,8S,10R,13S)-2-Debenzoyl-10-deacetyl-2-(3-fluoro-benzo-yl)-7,10-bis-(2,2,2-trichloro-eth-oxy-carbon-yl)baccatin III ethyl acetate monosolvate monohydrate.
| S-EPMC3051954 | biostudies-literature
Unknown (1S,3S,8R,9S,10R)-9,10-Ep-oxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodeca-ne.
| S-EPMC3998592 | biostudies-literature
Unknown (1R,2R,5R,6S,9R,10S,13S,14S,18R)-1,6,7,8,9,14,15,16,17,17,18-Undeca-chloro-penta-cyclo-[12.2.1.1.0.0]octa-deca-7,15-diene.
| S-EPMC2961815 | biostudies-literature
Unknown (3R,4S,5S,8S,10R,13R)-3-Hy-droxy-kaura-9(11),16-dien-18-oic acid.
| S-EPMC3275267 | biostudies-literature